Pawling Real Estate

Are you looking to settle down in a community that offers top-notch education for your children? Look no further than the charming town of Pawling, nestled in the heart of Dutchess County, New York. The Pawling school district is renowned for its commitment to academic excellence and holistic development of students.

With a strong emphasis on creating a nurturing environment for learning, the Pawling school district boasts a team of dedicated educators who are passionate about helping students reach their full potential. From innovative teaching methods to a wide range of extracurricular activities, students in Pawling are provided with the tools they need to succeed both inside and outside the classroom.

Families are drawn to Pawling not only for its excellent schools but also for its picturesque surroundings and tight-knit community. Imagine living in a place where your children can receive a top-quality education while exploring the great outdoors and forming lifelong friendships.

Whether you're looking to buy a home near top-rated schools or simply want to be part of a community that values education, Pawling has something to offer for everyone. Come and discover the beauty of Pawling – where academic excellence meets small-town charm.

Newest Listings in Pawling

$774,900

3 Beds ⋅ 3 Baths ⋅ H6323765 MLS

EXQUISITE Bi-level Colonial custom-built in 2021. This ENERGY EFFICIENT & ECO friendly home is an ideal blend of country design with modern characteristics. Situated on 2 ACRES of private level all fenced-in land w/a long driveway, lush lawns and beautiful gardens with patios & decks, a swimming pool, and breathtaking views of the countryside. Enter through a mahogany door to the 2-story foyer and continue to upper floor where you'll find an elegant living space w/vaulted ceilings and an open floor plan consisting of a gourmet kitchen that boasts white quartz countertops, S/S appliances, an oversized island overlooking the dining area w/double glass doors leading to Trex deck, living rm w/propane fireplace, grand suite with walk-in barn door closet, and a luxurious bath with stall shower. There are two additional bedrooms, and a hall bath with a bathtub. The lower floor consists of an oversized family rm with glass door to the back yard, full bath, small laundry room, and 2-car garage. This home features stained hardwood floors, heated tile floors throughout, Sonos multi-room sound and ceiling audio speakers, central vacuum, Lutron lighting control, ATD security system, generator, energy-efficient insulation, artificial Turf in the back yard, above ground swimming pool with Trex deck, fenced-in front and back yard, LeafGuard gutter system, and even more. Relax, enjoy, and entertain guests with scenic mountain views from the gorgeous poolside or up on the new deck. A true gem!

25 Liberty Lane, Holmes

$514,000

3 Beds ⋅ 2 Baths ⋅ H6324994 MLS

Your search is over! Charming 3 bedrm, 2 bath home on 1.15 acres, fenced-in private yard, perfect for your little ones or four-legged family members enjoy nature in safety. Savor morning coffee on the wrap-around deck overlooking tranquil gardens, beautiful natural landscaping & your own greenhouse! Bright open floor plan w/cathedral ceilings, hardwoods make this home feel like an artist's retreat. Enjoy the like-new kitchen w/stainless appliances, granite counters & relax at night in the beautiful sunken master suite w/walk-in closet, private bath, slider to private deck! Large finished walk-out basement w/ laundry rm & access to 1 car garage. Just outside the quaint village of Pawling, you'll enjoy complete privacy in your own hidden oasis only a few minutes to Rt 22 & Metro North, shops, restaurants, parks, trails, golf & skiing. Perfect for nature-lovers, garden enthusiasts, artists & young families. Your Hudson Valley Retreat Awaits!

45 Fenwood Drive, Pawling

$375,000

2 Beds ⋅ 1 Baths ⋅ H6324001 MLS

Snuggled of 3+ acres of land, this beautiful Cottage offers a world of opportunity. You will arrive to the rocking chair front porch and into the Kitchen that is flooded with natural light, a large closet with stack washer and dryer. Continuing through you enter the beautiful stone fireplace with woodburning stove insert, hardwood floors and ceiling fan, off the living room you will find a sun filled family room with hardwood floors and French doors to the back deck. The main floor also offers a large bedroom with Glass door, double closets and ceiling fan, full bathroom with new flooring, and a second bedroom with hardwood floors. This home also offers a free span walk up attic with plenty space. The 3.1 acres offers abundant space for a potential homesteader or nature lover. The large shed offers additional storage space and a wood stove hookup. Also found on the property is an old outhouse and a washhouse. Located minutes from the Rail trail and Appalachian Trail, this property is an outdoor lovers dream.

79 N White Rock Road, Holmes

$725,000

3 Beds ⋅ 3 Baths ⋅ H6323968 MLS

Minutes from the Village of Pawling, this custom built 3-bedroom 3-bathroom Colonial is Perched on 1.5+ acres. Pull up the wandering drive and you will be welcome by the large, tiled entry. To the right you will find a large open, eat-in kitchen with center island, granite countertops and a walk out to the back patio. Through the kitchen you will enter the large formal dining room with hardwood floors, large bay window and ample room for entertaining. Through French doors from the Dining Room or through the kitchen you will enter the Living Room featuring hardwood floors, large windows and sliding glass doors to the patio. To the left of the entry, you will find the sunlight flooded formal living room with hardwood floors, corner fireplace. The main floor also offers a full bath. Up the center stairs you will find the primary suite boasting soaring ceilings, large windows, hardwood floors, walk in closet and a primary bath. Down the hall you will pass a large full bathroom and two additional bedrooms with hardwood floors and large closets. Passing through the left bedroom you will find a large bonus room with carpeted floors, large closets and tons of space! Additionally, there is a full unfinished basement with laundry and a large 2 car garage. Located conveniently near Metro-North, Route 55, Route 22, I684 and I84. A must see!

1 Noel Court, Pawling

$595,000

5 Beds ⋅ 3 Baths ⋅ H6323998 MLS

Single family 5 bedroom, 3 bath country home. Secluded in the woods, but close to town. 10.39 acres with pool and 2 paddock barn offering a unique experience for those desiring privacy and a connection to nature. Small bungalow in back perfect for an office or recreational area.

130 Old Route 55, Pawling

$510,000

3 Beds ⋅ 3 Baths ⋅ H6323138 MLS

Welcome to this beautifully maintained raised ranch, offering the perfect blend of comfort and style. Step inside to discover gleaming hardwood floors that flow throughout the main floor living areas and bedrooms, creating a warm and inviting atmosphere. The heart of this home is the renovated kitchen, featuring stainless steel appliances, granite countertops, ample cabinetry, a peninsula for seating that is perfect for both everyday meals and entertaining guests. Open concept Living Room-Dining Room has sliding glass doors that open to multi-level deck. Primary Bedroom has a full bathroom with walk-in shower and walk-in closet. On the lower level you will find a family room completewith summer kitchen, full bath and sliding glass doors leading out to screened in porch. Three level deck looks into private backyard and is a perfect place to relax, dine, and take in the serene surroundings, whether you're sipping your morning coffee or hosting a barbecue! Also on the lower level you will find the Laundry/Utility room as well as a bonus storage room adjacent to the one car garage! Taxes do not reflect S.T.A.R.

184 South Road, Holmes

$439,999

3 Beds ⋅ 2 Baths ⋅ H6323410 MLS

Welcome to your dream home in the charming Village of Pawling! This delightful 3-bedroom, 1.5-bathroom house offers the perfect blend of comfort and convenience. Step inside and be greeted by a spacious eat-in kitchen, boasting elegant granite countertops that will inspire your inner chef. The primary bedroom, complete with its own half bath, provides a peaceful retreat after a long day. All bedrooms are conveniently located on the main level, ensuring easy access for all ages. Need a little extra space? The large sun room is perfect for relaxation or entertaining, with a deck that leads to an inviting above-ground pool perfect for those hot summer days! Storage won't be an issue here, with multiple sheds dotting the property and a full walkout basement offering plenty of room for all your belongings. The large backyard, completely fenced in, provides a safe haven for kids and pets to play to their hearts' content. Location is key, and this property doesn't disappoint. Golf enthusiasts will appreciate the proximity to the local course, while commuters will love being close to the Metro North train station. For winter sports fans, Thunder Ridge Ski Area is just a short drive away. Foodies, rejoice! The renowned McKinney & Doyle fine dining establishment is nearby, perfect for those special nights out. Whether you're lounging by the pool, hosting a barbecue on the deck, or simply enjoying the serenity of your new home, this property offers something for everyone. Don't miss out on this fantastic opportunity to make your home in the heart of Pawling where small-town charm meets modern convenience!

85 Fairway Drive, Pawling

$739,000

5 Beds ⋅ 4 Baths ⋅ H6322488 MLS ⋅ The Highlands BLDG.

Welcome to this stunning example of refined elegance and timeless charm! This impressive colonial home features 5 spacious bedrooms and 4 beautifully appointed bathrooms. The oversized windows allow for an abundance of light displaying the high ceilings and hardwood floors that extend throughout the home. The gourmet kitchen features stainless steel appliances and a large island with seating perfect for preparing meals and entertaining guests. At the end of the day, retreat to the Primary bedroom with a spa-like en suite bathroom and walk-in closet. Each additional bedroom is thoughtfully designed with ample closet space as well. Step outside to the beautifully landscaped backyard with a deck perfect for outdoor gatherings and relaxation. The tastefully finished walk-out basement includes the 5th bedroom, a cozy office, and 4th full bathroom. This residence offers luxury, comfort, and plenty of space in a serene setting. Come enjoy the community Tennis courts and heated pool!

26 Chestnut Lane, Pawling

$16,900,000

4 Beds ⋅ 4 Baths ⋅ H6321514 MLS ⋅ Quaker Hill BLDG.

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, Grand Prix polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.

15 Kirby Hill Road, Pawling

$150,000

H6322307 MLS ⋅ Cushman Farms BLDG.

Explore this exceptional 4+ acre level lot on Estate Drive, nestled further into the peaceful Cushman Road subdivision in Pawling, NY. Enjoy the privacy of this serene setting while benefiting from shared access with two other similar properties via a common driveway. This lot is equipped with underground utilities and a well, offering a smooth building process. Located just 6 minutes from the charming Village of Pawling, you'll have easy access to delightful cafes, boutique shops, fine dining, and Metro-North Railroad's Harlem Line. Embrace the opportunity to create your ideal home in this tranquil, well-maintained community.

Estate Drive, Pawling

$150,000

H6322305 MLS ⋅ Cushman Farms BLDG.

Discover the perfect blend of privacy and convenience with this exceptional corner lot in the exclusive Cushman Farms subdivision, located in the heart of the beautiful Hudson Valley. This over 5-acre property is Board of Health Approved and offers easy access to all essential utilities. Nestled in a peaceful and remote setting, it provides the tranquility and seclusion you desire, while being just a short 6-minute drive to the charming village of Pawling. Enjoy vibrant community amenities, including cafes, fine dining, and boutiques, with convenient access to the Metro-North Railroad for easy commuting. Don't miss this rare opportunity to own a piece of paradise in one of New York's most picturesque regions.

Cushman Road, Pawling

$150,000

H6322234 MLS ⋅ Cushman Farms BLDG.

Discover the perfect spot for your dream home with this 4+ acre cleared corner lot on Cushman Road, Pawling, NY. Located at the manicured entrance of Cushman Farms and just 6 minutes from the vibrant Village of Pawling, this property offers the ideal blend of serenity and convenience. Enjoy the privacy of a backcountry setting with underground utilities, a well, and easy access to charming cafes, boutique shops, fine dining, and Metro-North Railroad's Harlem Line. Embrace this unique opportunity to create your own retreat in a beautifully maintained community.

Estate Drive, Pawling

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